1: 1-bromo-4-fluorobenzene With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate in tetrahydrofuran Negishi Coupling; 0.0833333 h; Schlenk techniqueInert atmosphere; 2: 4-ethoxy-4-oxobutylzinc bromide lithium chloride in tetrahydrofuran T=50°C; Negishi Coupling; 2 h; Schlenk techniqueInert atmosphere;

pyridine; N,N'-dimethyl-N,N'-propyleneurea; 1,10-phenanthroline; NiI2*3.5H2O; sodium iodide; zinc T=20 - 60°C; 19 h; chemoselective reaction;

1: AlCl3 2: (reduction) View Scheme

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1: (reduction) View Scheme

Multistep reaction;

1: 85 percent / LiAlH4 / diethyl ether / Heating 2: PBr3 / 1) -30 deg C, 2) r.t., 24 h View Scheme

1: 85 percent / LiAlH4 / diethyl ether / Heating 2: PBr3 / 1) -30 deg C, 2) r.t., 24 h 3: 55 percent View Scheme

1: 85 percent / LiAlH4 / diethyl ether / Heating 2: PBr3 / 1) -30 deg C, 2) r.t., 24 h 3: 55 percent 4: 82 percent / KOH / ethanol; H2O / 6 h / Heating View Scheme

lithium aluminium tetrahydride in diethyl ether Heating;